N-acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate.
Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h.
Nechab
Malek
M
Laboratoire de Chimie Moléculaire Organique, LCP UMR 6264, Boite 562, Université Paul Cézanne, Aix-Marseille III, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, 13397, Marseille Cedex 20, France.
El Blidi
Lahssen
L
Vanthuyne
Nicolas
N
Gastaldi
Stéphane
S
Bertrand
Michèle P
MP
Gil
Gérard
G
D000588:Amines / Q000378:metabolism*; D055162:Biocatalysis; D004952:Esters / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000378:metabolism*; D007700:Kinetics; D012697:Serine Endopeptidases / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D000588:Amines; D004952:Esters; D012697:Serine Endopeptidases; D005998:Glycine